26429-97-0

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 5927-18-4 trimethyl phosphonoacetate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 116-54-1 dichloroacetic acid methyl ester 
• 65-85-0 benzoic acid 
• 80-70-6 N,N,N',N'-tetramethylguanidine 
• 96-32-2 bromoacetic acid methyl ester 
• 18328-11-5 3-benzyl propionaldehyde 
• 1382786-56-2 methyl 3-chloro-5-phenylpentanoate 
• 1382786-54-0 2-chloro-2-(2-chloro-4-phenylbutyl)malononitrile 
• 67-56-1 methanol 
• 24271-22-5 5-phenyl-2(E)-pentenoic acid 

Downstream Products

• 75553-23-0 (E)-5-phenyl-2-penten-1-ol 
• 138797-07-6 3,4-Diphenethyl-hexanedioic acid dimethyl ester 
• 126175-28-8 methyl 4-(N,N'-bis(ethoxycarbonyl)hydrazino)-5-phenyl-2-pentenoate 
• 129042-96-2 methyl N-benzyl-3-amino-5-phenylpentanoate 
• 99439-81-3 (-)-methyl 3-methyl-5-phenylpentanoate 

Relevant academic research and scientific papers

Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes

The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.

Remote Functionalization of α,β-Unsaturated Carbonyls by Multimetallic Sequential Catalysis

The remote functionalization of α,β-unsaturated carbonyls by an array of multimetallic sequential catalytic systems is described. The reactions are triggered by hydrometalation using [Pd-H] or [Ru-H] isomerization catalysts and driven by the formation of thermodynamically more stable 1,2-vinyl arenes. The Pd-catalyzed deconjugative isomerization was combined with a Cu-catalyzed β-borylation of the transiently generated styrenyl derivatives to deliver a range of products that would not be accessible with the use of a single catalyst. [Pd/Cu] catalytic systems were also identified for the highly enantioselective α-hydroboration and α-hydroamination of the styrenyl intermediates. Difunctionalization simultaneously at the benzylic and homobenzylic positions was achieved by combining the isomerization process with Sharpless asymmetric dihydroxylation (SAD) using [Pd/Os] or [Ru/Os] couples. Starting from a simple α,β-unsaturated ester, an isomerization/dihydroxylation/lactonization sequence gave access to a naturally occurring γ-butyrolactone in good yield, with excellent diastereo- and enantioselectivity.

Formation of Enol Ethers by Radical Decarboxylation of α-Alkoxy β-Phenylthio Acids

Enol ethers are formed by radical decarboxylation of α-alkoxy β-phenylthio acids via the corresponding Barton esters. The phenylthio acids were usually made by the known regioselective reaction of α,β-epoxy acids with PhSH in the presence of InCl3, followed by O-alkylation of the resulting alcohol. In one case, thiol addition to an α,β-unsaturated ethoxymethyl ester was used.

Phosphetane oxides as redox cycling catalysts in the catalytic wittig reaction at room temperature

Recently, phosphorus redox cycling has gained significant importance for a number of transformations originally requiring the use of stoichiometric amounts of phosphorus reagents. While these methodologies have several benefits, high catalyst loadings (≥10 mol percent) and harsh reaction conditions (T ≥ 100 °C) often limit their versatility and applicability. Herein, we report differently substituted phosphetane oxides as efficient catalysts for the catalytic Wittig reaction. The phosphetane scaffold is easy to modify, and a number of catalysts can be obtained in a simple two-step synthesis. The activity in the Wittig reaction significantly surpasses previously reported phospholane-based catalysts and the reaction can be conducted with catalyst loadings as low as 1.0 mol percent even at room temperature. Furthermore, a Br?nsted acid additive is no longer required to achieve high yields at these mild conditions. A methyl-substituted phosphetane oxide was employed to synthesize 25 different alkenes with yields of up to 97percent. The methodology has a good functional group tolerance and the reaction can be performed starting with alkyl chlorides, bromides, or iodides. Additionally, it was possible to use poly(methylhydrosiloxane) as the terminal reductant in the catalytic Wittig reaction employing 2-MeTHF as a renewable solvent. The intermediates of the Wittig reaction were analyzed by 31P NMR spectroscopy, and in situ NMR experiments confirmed phosphane oxide as the resting state of the catalyst. Further kinetic investigations revealed a striking influence of the base on the rate of phosphane oxide reduction.

Trifluoromethylation of Unactivated Alkenes with Me3SiCF3 and N-Iodosuccinimide

A novel approach to the trifluoromethylation of unactivated alkenes is presented. This reaction is promoted by N-iodosuccinimide (NIS) under visible light irradiation without the need for photocatalysts. The mild conditions allow the direct synthesis of u

The Catalytic Asymmetric Mukaiyama–Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters

α,β-Unsaturated esters are readily available but challenging substrates to activate in asymmetric catalysis. We now describe an efficient, general, and highly enantioselective Mukaiyama–Michael reaction of silyl ketene acetals with α,β-unsaturated methyl esters that is catalyzed by a silylium imidodiphosphorimidate (IDPi) Lewis acid.

Synthesis and evaluation of (E)-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists

Novel series of compounds consisting of 2-amidocyclohex-1-ene carboxylate and phenyl parts which are connected by enyne (compounds 2a–f), but-1-yne (compounds 4a–j), and phenylethylene (compounds 5a–f) linkers as HCA2 full agonists were designed and their

Dual Palladium(II)/Tertiary Amine Catalysis for Asymmetric Regioselective Rearrangements of Allylic Carbamates

The streamlined catalytic access to enantiopure allylic amines as valuable precursors towards chiral β- and γ-aminoalcohols as well as α- and β-aminoacids is desirable for industrial purposes. In this article an enantioselective method is described that transforms achiral allylic alcohols and N-tosylisocyanate in a single step into highly enantioenriched N-tosyl protected allylic amines via an allylic carbamate intermediate. The latter is likely to undergo a cyclisation-induced [3,3]-rearrangement catalysed by a planar chiral pentaphenylferrocene palladacycle in cooperation with a tertiary amine base. The otherwise often indispensable activation of palladacycle catalysts by a silver salt is not required in the present case and there is also no need for an inert gas atmosphere. To further improve the synthetic value, the rearrangement was used to form dimethylaminosulfonyl-protected allylic amines, which can be deprotected under non-reductive conditions.

Toward a Unified Mechanism for Oxoammonium Salt-Mediated Oxidation Reactions: A Theoretical and Experimental Study Using a Hydride Transfer Model

A range of oxoammonium salt-based oxidation reactions have been explored computationally using density functional theory (DFT), and the results have been correlated with experimentally derived trends in reactivity. Mechanistically, most reactions involve a formal hydride transfer from an activated C-H bond to the oxygen atom of the oxoammonium cation. Several new potential modes of reactivity have been uncovered and validated experimentally.

Phospholane-catalyzed wittig reaction

We identified 2-phenylisophosphindoline 2-oxide as a suitable and potentially tunable catalyst for the catalytic Wittig reaction of aldehydes with activated organohalides. This catalyst was obtained by a straightforward two-step synthesis. Trimethoxysilane proved to be an efficient reducing agent for the in situ generation and regeneration of the catalyst from the corresponding phosphane oxide. Sodium carbonate was identified as a suitable base for the transformation. It is noteworthy that the particle size of the sodium carbonate had a tremendous effect on the outcome of the reaction. Under the optimized reaction conditions, 23 aldehydes were converted into the corresponding alkenes in high isolated yields of up to 88%. Moreover, an asymmetric catalytic Wittig reaction was performed for the desymmetrization of a prochiral diketone.